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Suppose I strongly expect, based on material non-public information, that a public United States company in which I hold incentive stock options (as a current or former employee) will see an increase in its stock price in the next few months. In order to minimize my alternative minimum tax (AMT) liability, or avail of some other benefit (e.g., start the clock for long-term capital gains tax treatment based on where I expect the price to be in a year from now -- based on material non-public information), I choose to exercise my stock options right now, while the publicly estimated fair market value (i.e., the stock price) is relatively low. Could this be considered insider trading?

My understanding is that since the exercise of stock options is a transaction between me and the company, and I do not hold any material information the company does not hold, that transaction should not be considered insider trading (i.e., insider trading requires an information asymmetry between the parties involved; if both parties are privy to the material non-public information, it's not insider trading). [Assume for the sake of this hypothetical that I don't have very deep inside information that is unavailable to the management/executives of the company.]

However, if we construe the parties involved to include taxing authorities (in this case, the United States federal government) it could be argued that by exercising my stock options now, I am unfairly using my inside information about the trajectory of the stock price to make money at the expense of the United States federal government. Or, if we construe the parties involved to include other shareholders, even ones I am not transacting with, then it could be argued that by exercising my stock options right now, I am affecting the stock price.

Could either of these arguments hold water, or is it fairly clear that this is not a case of insider trading?

Follow-up question: could the disclosure of the exercise of incentive stock options in a public company be considered the disclosure of material non-public information?

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  • My guess at why this wouldn't be insider trading of any kind is that stock options (as I'm aware of them) always execute at the same price: your "secret knowledge" neither affects that price or tells you how the price is likely to change (because it won't change), so it gives you no advantage over someone without that knowledge.
    – TripeHound
    Aug 29 '20 at 22:34
  • @TripeHound I think the issue the OP is worried about is that with ISOs, the amount of ordinary income realized is a function of the market price at the time of exercise. (Although if you hold it long enough, the entire spread is treated as capital gains instead, so the market price isn't really relevant.) That said, I think the answer is the same as for an ordinary stock purchase: you can't make decisions based on inside information. So the question is, does the OP have inside information?
    – chepner
    Aug 30 '20 at 12:38

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